#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:08:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179615 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/79/4507912.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4507912
loop_
_publ_author_name
'Hou, Guang-Feng'
'Li, Hong-Xing'
'Li, Wei-Zuo'
'Yan, Peng-Fei'
'Su, Xiao-Hong'
'Li, Guang-Ming'
_publ_section_title
;
 Two Series of Luminescent Flexible Polycarboxylate Lanthanide
 Coordination Complexes with Double Layer and Rectangle Metallomacrocycle
 Structures
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3374
_journal_paper_doi               10.1021/cg400174r
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C12 H22 Ce N O13'
_chemical_formula_sum            'C12 H22 Ce N O13'
_chemical_formula_weight         528.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                70.18(3)
_cell_angle_beta                 71.73(3)
_cell_angle_gamma                67.28(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4465(19)
_cell_length_b                   9.830(2)
_cell_length_c                   11.903(2)
_cell_measurement_reflns_used    8534
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      3.33
_cell_volume                     937.7(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_collection       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9256
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.494
_exptl_absorpt_correction_T_max  0.6187
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             526
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.238
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0353P)²+1.3063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                4031
_reflns_number_total             4266
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400174r_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        937.8(3)
_cod_database_code               4507912
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3866(4) 0.6414(4) 0.6121(3) 0.0249(6) Uani 1 1 d .
C2 C 0.2533(4) 0.7560(4) 0.5757(3) 0.0327(7) Uani 1 1 d .
H2 H 0.1549 0.7438 0.6121 0.039 Uiso 1 1 calc R
C3 C 0.2656(4) 0.8869(4) 0.4867(3) 0.0343(8) Uani 1 1 d .
H3 H 0.1756 0.9613 0.4634 0.041 Uiso 1 1 calc R
C4 C 0.4114(4) 0.9087(4) 0.4313(3) 0.0278(6) Uani 1 1 d .
C5 C 0.5442(4) 0.7990(4) 0.4676(3) 0.0253(6) Uani 1 1 d .
H5 H 0.6419 0.8132 0.4319 0.030 Uiso 1 1 calc R
C6 C 0.5320(4) 0.6659(4) 0.5584(3) 0.0261(6) Uani 1 1 d .
H6 H 0.6219 0.5930 0.5831 0.031 Uiso 1 1 calc R
C7 C 0.5581(4) 1.0634(4) 0.2762(3) 0.0281(7) Uani 1 1 d .
H7A H 0.6206 0.9818 0.2358 0.034 Uiso 1 1 calc R
H7B H 0.6147 1.0604 0.3329 0.034 Uiso 1 1 calc R
C8 C 0.5337(4) 1.2153(4) 0.1822(3) 0.0261(6) Uani 1 1 d .
C9 C 0.2333(4) 0.4670(4) 0.7206(3) 0.0273(6) Uani 1 1 d .
H9A H 0.2588 0.3571 0.7483 0.033 Uiso 1 1 calc R
H9B H 0.2030 0.4979 0.6428 0.033 Uiso 1 1 calc R
C10 C 0.0924(4) 0.5366(4) 0.8116(3) 0.0252(6) Uani 1 1 d .
C11 C 0.5184(4) 0.3818(4) 0.7196(3) 0.0254(6) Uani 1 1 d .
H11A H 0.5909 0.3781 0.6414 0.031 Uiso 1 1 calc R
H11B H 0.4953 0.2861 0.7525 0.031 Uiso 1 1 calc R
C12 C 0.5968(3) 0.3982(4) 0.8057(3) 0.0240(6) Uani 1 1 d .
N1 N 0.3739(3) 0.5053(3) 0.7004(2) 0.0264(6) Uani 1 1 d .
O1 O 0.5135(3) 0.4270(3) 0.90666(19) 0.0276(5) Uani 1 1 d .
O2 O 0.7408(3) 0.3795(3) 0.7804(2) 0.0372(6) Uani 1 1 d .
O3 O 0.1046(3) 0.6043(3) 0.8786(2) 0.0323(5) Uani 1 1 d .
O4 O -0.0334(3) 0.5178(3) 0.8146(2) 0.0368(6) Uani 1 1 d .
O5 O 0.4103(3) 1.0418(3) 0.3415(2) 0.0341(5) Uani 1 1 d .
O6 O 0.3972(3) 1.2978(3) 0.1724(2) 0.0324(5) Uani 1 1 d .
O7 O 0.6599(3) 1.2432(3) 0.1216(2) 0.0349(6) Uani 1 1 d .
O8 O 0.7644(3) 0.6997(3) 0.9984(3) 0.0427(6) Uani 1 1 d .
H81 H 0.8530 0.7134 0.9637 0.064 Uiso 1 1 d R
H82 H 0.6902 0.7821 0.9829 0.064 Uiso 1 1 d R
O9 O 0.9665(4) 0.2111(4) 0.9510(3) 0.0614(9) Uani 1 1 d .
H91 H 1.0088 0.1787 0.8867 0.092 Uiso 1 1 d R
H92 H 0.9723 0.1383 1.0151 0.092 Uiso 1 1 d R
O10 O 0.9707(6) 0.7681(6) 0.3490(4) 0.115(2) Uani 1 1 d .
H101 H 1.0436 0.6894 0.3317 0.172 Uiso 1 1 d R
H102 H 0.9337 0.7618 0.4248 0.172 Uiso 1 1 d R
O11 O 0.1327(4) 0.2963(5) 0.4056(3) 0.0716(12) Uani 1 1 d .
H111 H 0.2237 0.2573 0.3660 0.107 Uiso 1 1 d R
H112 H 0.0844 0.3783 0.3604 0.107 Uiso 1 1 d R
O12 O 0.0295(8) 0.9740(7) 0.8064(6) 0.173(4) Uani 1 1 d .
H122 H 0.0746 1.0321 0.7482 0.260 Uiso 1 1 d R
H121 H -0.0571 0.9827 0.7926 0.260 Uiso 1 1 d R
O13 O 0.464(5) -0.014(6) 0.045(3) 0.24(2) Uiso 0.338(14) 1 d P
O13' O 0.2885(10) 0.0032(10) 0.1629(8) 0.108(4) Uiso 0.662(14) 1 d P
Ce1 Ce 0.738029(17) 0.462251(19) 0.969114(14) 0.02153(7) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 117.9(3) . .
C6 C1 N1 121.3(3) . .
C2 C1 N1 120.8(3) . .
C3 C2 C1 121.1(3) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
C2 C3 C4 120.7(3) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C5 C4 O5 124.9(3) . .
C5 C4 C3 119.3(3) . .
O5 C4 C3 115.8(3) . .
C4 C5 C6 120.1(3) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C1 C6 C5 120.9(3) . .
C1 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
O5 C7 C8 110.1(3) . .
O5 C7 H7A 109.6 . .
C8 C7 H7A 109.6 . .
O5 C7 H7B 109.6 . .
C8 C7 H7B 109.6 . .
H7A C7 H7B 108.2 . .
O6 C8 O7 127.3(3) . .
O6 C8 C7 119.1(3) . .
O7 C8 C7 113.7(3) . .
N1 C9 C10 116.5(3) . .
N1 C9 H9A 108.2 . .
C10 C9 H9A 108.2 . .
N1 C9 H9B 108.2 . .
C10 C9 H9B 108.2 . .
H9A C9 H9B 107.3 . .
O3 C10 O4 124.0(3) . .
O3 C10 C9 121.3(3) . .
O4 C10 C9 114.6(3) . .
N1 C11 C12 113.1(3) . .
N1 C11 H11A 109.0 . .
C12 C11 H11A 109.0 . .
N1 C11 H11B 109.0 . .
C12 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
O2 C12 O1 120.2(3) . .
O2 C12 C11 121.3(3) . .
O1 C12 C11 118.4(3) . .
O2 C12 Ce1 60.28(17) . .
O1 C12 Ce1 60.43(16) . .
C11 C12 Ce1 174.7(2) . .
C1 N1 C9 117.0(3) . .
C1 N1 C11 117.7(2) . .
C9 N1 C11 118.3(3) . .
C12 O1 Ce1 150.8(2) . 2_667
C12 O1 Ce1 94.74(18) . .
Ce1 O1 Ce1 109.31(9) 2_667 .
C12 O2 Ce1 95.29(19) . .
C10 O3 Ce1 135.6(2) . 2_667
C10 O4 Ce1 137.9(2) . 1_455
C4 O5 C7 117.6(3) . .
C8 O6 Ce1 138.4(2) . 2_676
C8 O7 Ce1 137.2(2) . 1_564
Ce1 O8 H81 114.0 . .
Ce1 O8 H82 115.9 . .
H81 O8 H82 110.7 . .
Ce1 O9 H91 125.6 . .
Ce1 O9 H92 116.8 . .
H91 O9 H92 111.6 . .
H101 O10 H102 115.0 . .
H111 O11 H112 110.2 . .
H122 O12 H121 110.2 . .
O13 O13 O13' 157(6) 2_655 .
O1 Ce1 O3 96.32(8) 2_667 2_667
O1 Ce1 O4 144.54(9) 2_667 1_655
O3 Ce1 O4 86.21(8) 2_667 1_655
O1 Ce1 O7 74.14(9) 2_667 1_546
O3 Ce1 O7 78.22(9) 2_667 1_546
O4 Ce1 O7 140.24(9) 1_655 1_546
O1 Ce1 O6 74.54(8) 2_667 2_676
O3 Ce1 O6 136.55(9) 2_667 2_676
O4 Ce1 O6 79.46(9) 1_655 2_676
O7 Ce1 O6 135.18(8) 1_546 2_676
O1 Ce1 O8 75.42(9) 2_667 .
O3 Ce1 O8 67.73(9) 2_667 .
O4 Ce1 O8 72.93(10) 1_655 .
O7 Ce1 O8 130.74(9) 1_546 .
O6 Ce1 O8 68.86(9) 2_676 .
O1 Ce1 O9 144.12(10) 2_667 .
O3 Ce1 O9 70.58(11) 2_667 .
O4 Ce1 O9 69.79(11) 1_655 .
O7 Ce1 O9 70.55(10) 1_546 .
O6 Ce1 O9 137.72(11) 2_676 .
O8 Ce1 O9 124.82(11) . .
O1 Ce1 O2 118.69(8) 2_667 .
O3 Ce1 O2 140.80(8) 2_667 .
O4 Ce1 O2 75.45(8) 1_655 .
O7 Ce1 O2 94.05(9) 1_546 .
O6 Ce1 O2 74.13(9) 2_676 .
O8 Ce1 O2 134.68(9) . .
O9 Ce1 O2 70.62(11) . .
O1 Ce1 O1 70.69(9) 2_667 .
O3 Ce1 O1 148.89(8) 2_667 .
O4 Ce1 O1 121.03(8) 1_655 .
O7 Ce1 O1 71.12(8) 1_546 .
O6 Ce1 O1 68.73(8) 2_676 .
O8 Ce1 O1 131.03(9) . .
O9 Ce1 O1 103.03(10) . .
O2 Ce1 O1 49.12(7) . .
O1 Ce1 C12 94.53(8) 2_667 .
O3 Ce1 C12 155.46(9) 2_667 .
O4 Ce1 C12 97.50(8) 1_655 .
O7 Ce1 C12 83.72(9) 1_546 .
O6 Ce1 C12 67.72(9) 2_676 .
O8 Ce1 C12 136.55(9) . .
O9 Ce1 C12 87.87(11) . .
O2 Ce1 C12 24.42(7) . .
O1 Ce1 C12 24.82(7) . .
O1 Ce1 Ce1 36.93(5) 2_667 2_667
O3 Ce1 Ce1 127.58(6) 2_667 2_667
O4 Ce1 Ce1 143.89(6) 1_655 2_667
O7 Ce1 Ce1 68.47(7) 1_546 2_667
O6 Ce1 Ce1 67.17(6) 2_676 2_667
O8 Ce1 Ce1 105.64(7) . 2_667
O9 Ce1 Ce1 128.37(9) . 2_667
O2 Ce1 Ce1 82.30(6) . 2_667
O1 Ce1 Ce1 33.77(5) . 2_667
C12 Ce1 Ce1 57.91(6) . 2_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.398(4) .
C1 C2 1.399(5) .
C1 N1 1.414(4) .
C2 C3 1.381(5) .
C2 H2 0.9300 .
C3 C4 1.394(5) .
C3 H3 0.9300 .
C4 C5 1.379(5) .
C4 O5 1.379(4) .
C5 C6 1.405(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 O5 1.427(4) .
C7 C8 1.516(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 O6 1.248(4) .
C8 O7 1.263(4) .
C9 N1 1.445(4) .
C9 C10 1.520(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O3 1.253(4) .
C10 O4 1.259(4) .
C11 N1 1.455(4) .
C11 C12 1.520(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 O2 1.250(4) .
C12 O1 1.268(4) .
C12 Ce1 3.010(3) .
O1 Ce1 2.431(2) 2_667
O1 Ce1 2.627(2) .
O2 Ce1 2.626(3) .
O3 Ce1 2.461(2) 2_667
O4 Ce1 2.467(2) 1_455
O6 Ce1 2.522(3) 2_676
O7 Ce1 2.493(2) 1_564
O8 Ce1 2.586(3) .
O8 H81 0.8500 .
O8 H82 0.8500 .
O9 Ce1 2.599(3) .
O9 H91 0.8500 .
O9 H92 0.8500 .
O10 H101 0.8500 .
O10 H102 0.8501 .
O11 H111 0.8501 .
O11 H112 0.8500 .
O12 H122 0.8500 .
O12 H121 0.8499 .
O13 O13 1.09(7) 2_655
O13 O13' 1.79(4) .
Ce1 O1 2.431(2) 2_667
Ce1 O3 2.461(2) 2_667
Ce1 O4 2.467(2) 1_655
Ce1 O7 2.493(2) 1_546
Ce1 O6 2.522(3) 2_676
Ce1 Ce1 4.1273(11) 2_667
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H121 O13' 0.85 2.04 2.838(12) 155.6 2_566
O12 H122 O10 0.85 1.87 2.582(8) 140.2 2_676
O11 H112 O4 0.85 2.10 2.839(4) 144.6 2_566
O11 H111 O6 0.85 2.38 3.099(4) 142.5 1_545
O11 H111 O5 0.85 2.21 2.948(5) 144.9 1_545
O10 H102 O11 0.85 1.87 2.707(6) 167.9 2_666
O10 H101 O2 0.85 2.06 2.781(5) 142.6 2_766
O9 H92 O12 0.85 2.03 2.847(7) 159.9 2_667
O9 H91 O10 0.85 2.63 3.379(6) 147.4 2_766
O9 H91 O12 0.85 2.43 3.123(10) 139.8 1_645
O8 H82 O13 0.85 2.42 3.19(5) 151.9 1_566
O8 H82 O13' 0.85 2.27 2.852(10) 126.3 2_666
O8 H82 O13 0.85 2.16 2.99(5) 166.2 2_666
O8 H81 O3 0.85 2.25 2.991(4) 145.1 1_655
